Dimethyl Sulfide → 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

HRID 1244883

Reaktionsgleichung

Reaktionsgleichung von HRID 1244883
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C1([B:15]2[O:23][C:20]([CH3:22])([CH3:21])[C:17]([CH3:19])([CH3:18])[O:16]2)C=CC=CC=1.IC1C=C(O)C=CC=1.BrC1C=CC(O)=CC=1.[B]1OC(C)(C)C(C)(C)O1.CSC.B.IC1C=CC(O)=CC=1>>[CH3:18][C:17]1([CH3:19])[C:20]([CH3:22])([CH3:21])[O:23][B:15]([C:6]2[CH:5]=[CH:4][C:3]([OH:8])=[CH:2][CH:7]=2)[O:16]1

Komponenten

9

Edukt 8

HCID 1068Dimethyl SulfideHCID 6331BoraneHCID 78084-Bromophenol2×HCID 107842-IodophenolHCID 108944-IodophenolHCID 122723-IodophenolHCID 570673Phenylboronic acid pinacol esterHCID 6364989Pinacolborane

Produkt 1

HCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Versuchsvorschrift

The above reaction procedure used for 2-iodophenol was followed. The reaction was also faster, being again complete before the first sample for gc analysis was withdrawn after 1 h 50 min reaction time. The amount of phenylboronic acid pinacol ester was about that found in the 3-iodophenol reaction. The reaction in which 4-bromophenol is used as substrate is slower but does go to completion. Pinacolborane prepared in situ from the dimethylsulfide adduct of borane can also be used with both the 4-bromophenol and 4-iodophenol.

Aufarbeitung

  1. customThe above reaction procedure
  2. customwas withdrawn after 1 h 50 min
  3. customreaction time

Quellen und Nachweise

ORD-Eintrag
ord-8caec487d94943f6b75f1be9f8e9d4a4
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07122694B2

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